This invention relates to N-(heterocyclicaminocarbonyl)carbonyl-substituted benzothiophene- and benzofuransulfonamides which are useful as herbicides. The invention also includes novel sulfonamides and sulfonyl isocyanates used in preparing such compounds.
Netherlands Patent No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (I), and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA1 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA1 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom; PA1 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA1 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA1 W and Q are independently oxygen or sulfur; PA1 n is 0, 1 or 2; PA1 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA1 Z is methyl or methoxy; or their agriculturally suitable salts, provided that: PA1 R.sup.4 is substituted aryl; and PA1 Y is Cl, CH.sub.3, CH.sub.2 Cl, CHCl.sub.2 or CCl.sub.3. PA1 R.sup.4 is p-chloro or p-methylphenyl; PA1 R.sup.1 and R.sup.3 are C.sub.2 H.sub.5 or i-C.sub.3 H.sub.7 ; PA1 R.sup.2 is H; and PA1 Y is Cl or CH.sub.3. PA1 R.sup.1 is H, Cl, Br, NO.sub.2, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, CO.sub.2 R.sup.2, C(O)NR.sup.3 R.sup.4, SO.sub.2 R or SO.sub.2 NR.sup.6 R.sup.7 ; PA1 R.sup.2 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 R.sup.8 ; PA1 R.sup.3 is C.sub.1 -C.sub.4 alkyl; PA1 R.sup.4 is H, C.sub.1 -C.sub.4 alkyl or OCH.sub.3 ; or PA1 R.sup.3 and R.sup.4 can be taken together to form --(CH.sub.2).sub.4 --; PA1 R.sup.5 is C.sub.1 -C.sub.4 alkyl; PA1 R.sup.6 is C.sub.1 -C.sub.3 alkyl or OCH.sub.3 ; PA1 R.sup.7 is C.sub.1 -C.sub.3 alkyl; PA1 R.sup.8 is C.sub.1 -C.sub.3 alkyl substituted with 1-3 atoms of F, Cl, or Br; PA1 R.sup.9 is H, CH.sub.3, OCH.sub.3, Cl, Br or NO.sub.2 ; PA1 W is O or S; PA1 A is ##STR7## X is H, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, OCH.sub.2 CF.sub.3, CH.sub.2 OCH.sub.3 or Cl; PA1 Y is CH.sub.3 ; OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or SCH.sub.3 ; PA1 Z is N, CH, C--Cl, C--Br, C--CN, C--CH.sub.3, C--C.sub.2 H.sub.5, C--CH.sub.2 CH.sub.2 Cl or C--CH.sub.2 CH.dbd.CH.sub.2 ; PA1 Y.sup.1 is H, CH.sub.3, OCH.sub.3 or Cl; and PA1 Q is O or CH.sub.2 ; PA1 (1) when R.sup.4 or R.sup.6 is OCH.sub.3, then R.sup.3 or R.sup.7 is CH.sub.3 ; PA1 (2) the total number of carbon atoms of either R.sup.3 and R.sup.4, or R.sup.6 and R.sup.7, is less than or equal to 4; and PA1 (3) when X is Cl, then Z is CH. PA1 (1) Compounds of Formula I wherein Z is N or CH; and R.sup.1 is H, Cl, Br, NO.sub.2, C.sub.1 -C.sub.3 alkyl, CO.sub.2 R.sup.2, SO.sub.2 R.sup.5 or SO.sub.2 NR.sup.6 R.sup.7 ; PA1 (2) Compounds of Preferred (1) wherein R.sup.9 is H; PA1 (3) Compounds of Preferred (2) wherein R is H; PA1 (4) Compounds of Preferred (3) wherein PA1 (5) Compounds of Preferred (4) wherein W is S; PA1 (6) Compounds of Preferred (5) wherein R.sup.1 is Cl, Br, NO.sub.2, CO.sub.2 R.sup.2, SO.sub.2 R.sup.5 or SO.sub.2 NR.sup.6 R.sup.7 ; PA1 (7) Compounds of Preferred (6) wherein R.sup.1 is at the 2-position of the benzo[b]thiophene ring; and PA1 (8) Compounds of Preferred (7) wherein R.sup.1 is CO.sub.2 R.sup.2. PA1 Z is N or CH. ##STR10## wherein L is NCO; PA1 B is CO.sub.2 R.sup.2, SO.sub.2 R.sup.5, SO.sub.2 NR.sup.6 R.sup.7, Cl, Br, H, NO.sub.2, C.sub.1-C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; and PA1 R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.9 and W are as previously defined; PA1 (1) when R.sup.6 is OCH.sub.3, then R.sup.7 is CH.sub.3 ; and PA1 (2) the total number of carbon atoms of R.sup.6 and R.sup.7 is less than or equal to 4. ##STR11## wherein L is Cl or NH.sub.2 ; PA1 B.sup.1 is CO.sub.2 R.sup.2, SO.sub.2 R.sup.5, SO.sub.2 NR.sup.6 R.sup.7, C(O)NR.sup.3 R.sup.4, Cl, Br, NO.sub.2 or C.sub.2 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; and PA1 R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.9 and W are as previously defined; PA1 (1) when R.sup.4 or R.sup.6 is OCH.sub.3, then R.sup.3 or R.sup.7 is CH.sub.3 ; and PA1 (2) the toal number of carbon atoms of either R.sup.3 and R.sup.4, or R.sup.6 and R.sup.7, is less than or equal to 4. ##STR12## wherein M is H or alkali metal ion; and PA1 R, R.sup.9, W and A are as previously defined; PA1 R.sub.10 is methyl, ethyl or CH.sub.2 CF.sub.3 ; PA1 R.sub.11 is methyl or ethyl; and PA1 Z is CH or N. PA1 (a) The compound of Formula XXI can be suspended or dissolved in an alkanol solvent, R.sub.10 OH, in the presence of two equivalents of alkoxide, OR.sub.10. The alkoxide can be added directly as alkali metal or alkaline earth metal alkoxide or can be generated by the addition to the alkanol solvent of at least two equivalents of a base capable of generating alkoxide from the solvent. Suitable bases include, but are not limited to, the alkali and alkaline earth metals, their hydrides and tert-butoxides. For example, when R.sub.10 is methyl, the compound of Formula XXI could be suspended or dissolved in methanol in the presence of two equivalents of sodium methoxide. Alternatively, two equivalents of sodium hydride could be used in place of the sodium methoxide. PA1 (b) The compound of Formula XXI can be suspended or dissolved in an inert solvent in the presence of at least two equivalents of alkoxide, --OR.sub.10. Suitable inert solvents include, but are not limited to, acetonitrile, THF and dimethylformamide. The alkoxide may be added directly as alkali metal or alkaline earth metal alkoxide or may be generated from alkanol and a base as described in (a) above. For example, when R.sub.10 is methyl, the compound of Formula XXI could be suspended or dissolved in THF in the presence of two equivalents of sodium methoxide. Alternatively, two equivalents each of methanol and sodium hydride could be used instead of sodium methoxide.
Compounds of Formula (II), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974): ##STR2## wherein R is pyridyl.
In U.S. Pat. No. 4,127,405, compounds are disclosed of the general formula: ##STR3## wherein R.sub.1 is ##STR4## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA2 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA2 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA2 A is ##STR8## X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or CH.sub.2 OCH.sub.3 ; and Y is CH.sub.3 or OCH.sub.3 ;
In particular, the patent discloses ortho-substituted compounds wherein the substitution is C.sub.1 -C.sub.4 alkyl.
Argentine Patent No. 174,510 (issued Feb. 14, 1963 to Deutsche Gold und Silber) disclosed, among others, herbicidal compositions of sulfonylureas (i) ##STR5## wherein R.sup.1, R.sup.2 and R.sup.3 are independently H, alkyl or alkenyl;
Specifically taught are herbicidal sulfonylureas where
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, corn, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need exists for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.